Fourteen years later, the same friendships and rivalries are in full play among these old friends. Diggs's writer character, Harper, is desperate for his next hit book and thinks secretly profiling one of his famous friends while they're spending the holidays together might be the ticket to success.
Diggs sat down with Moviefone to talk about the highlights of making "The Best Man Holiday," which include performing a New Edition number, hanging out with the Buffalo Bills, and wine-fueled "Voice" viewing parties.
WARNING: Minor spoilers ahead!
Moviefone: How did making the first movie change your life?
Taye Diggs: Well, "The Best Man" is considered a classic, and it changed my life in that I was lucky enough to have it on my resumé. A lot of movies used "The Best Man" as kind of a model, and I was proud to be part of one of the first of its kind. I met some really great people that continue to be in my life, so I'm very big on friendship and relationships. To have experienced that movie with those people was special. And for me, as an actor, to be one of the leads in a movie like that, I also proved to myself that this wasn't a fluke, that I could do this and that I could have a good time doing it.
Had you stayed in touch with most of the cast?
We've all kept in contact just because it's a small industry and it's a small town. But that being said, it was really great to kind of go back to theater camp with them. It was different because we have families now, relationships; we had to deal with that. People were leaving on the weekends to see their kids. But when we did get together, it was a ball.
And everyone was happy to come back?
Oh, yeah. As far as I know. [Smiles]
You have that scene where you, Morris Chestnut, Terrence Howard, and Harold Perrineau lip-synch and dance to New Edition's "Can You Stand the Rain" for the ladies. Was that the most fun days you had on the set?
Yeah, that was one of the most fun. I love to dance, and Harold and I both have a dance background. So that was a ball. The way it was filmed, Malcolm was kind of brilliant, he made sure that we knew when we were filming, whether or not the cameras were on the girls, they would be there watching, so that we could get a real reaction from them. That added a certain element and put a certain spirit in the air. It was like live theater, we were performing for a live audience.
Did you already know all the words?
Oh, sure, sure. That added to the fun as well. All of us used to pretend we were a member of New Edition and would sing that song.
What about the football scenes? You get to be on the sidelines during a New York Giants game.
That was cool. That was the last day of shooting, and that was cool to be out there with some real players. I think we shot that in Buffalo or somewhere. We were standing where the Buffalo Bills actually play. Some of the Bills came and kicked it with us. It was a very cool experience. And to see your boy [Morris Chestnut] out there in a uniform, running patterns; it was tight.
This movie takes an unexpectedly sad turn. Are you worried that will throw audiences who are expecting a happy, upbeat holiday movie?
I know that the studio was worried early on, that they wanted more humor, but they signed off on this draft. And I think they're counting on people laughing when they're supposed to laugh but also getting emotionally invested as well. I feel like it's the type of emotional journey that people will enjoy. Sometimes I go to a movie and I just don't feel like crying. I'm hoping that people will just let themselves go and let themselves feel.
Was it heavy making the movie, or did you laugh a lot?
Both. Morris had the heavy lifting. He did just a spectacular job, I thought, of saving certain emotions for certain places. Outside of the heavy moments, we were laughing constantly. Sanaa was always snapping shots and putting them on Instagram. I always like to get people together and just ask really thought-provoking questions about life and spirituality and that always ends up with everyone cracking up. For some reason, "The Voice" was the show we all watched. We'd grab some wine and go watch "The Voice." Harold and I, we love to dance, so there was a lot of that going on. Movies like this, you just going to work because it's a lot of fun when the cameras aren't rolling and it continues to be fun when they are rolling.
Would you be up for a third "Best Man?"
I don't know. Sure. Absolutely. I'm still in the mindset of, "When I'm on set, I'll believe it." I had a ball making the first two and I'd love to do a third.
In the movie, Harper asks Lance what his three tenets are, and he answers "God, family, football." What are yours in your own life?
Friendship, humor, and loyalty.
Interesting, because Harper's really not all that loyal. Is that tough, to play a character who makes some really questionable decisions?
Those are the best characters to play; the ones that are kind of one-dimensional and all good, those are boring. Real actors want something that they can play against, you know what I mean? As an actor, you look for interesting characters, not boring, predictable characters. The bad guys are the ones that are just a little twisted, flawed, those are the ones that are the most fun to play.
You haven't played a villain very often.
Just a couple times. In "The Way of the Gun," I was a killer. And what was the movie that was similar to "The Matrix?"
Yeah, yeah, yeah. I was a bad guy in that.
You have a very famous scene in that...
Yeah, I get my face sliced off! [Grins] Yeah, all the actors that I know who enjoy acting just want to play a character who has more than one dimension. There are good guys who do bad things and bad guys who do good things and it's fun to play both.
"The Best Man Holiday" hits theaters Friday, November 15.
Can't wait until Friday? Send a Morris Chestnut Best Man Holiday Gram now, or check out Q and Shelby's Relationship Tumblr.